• Bulletin of the Korean Chemical Society
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• v.35 no.2
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• pp.562-568
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• 2014

In this work, synthesis, characterization and antimicrobial activity of series of imidazolines-oxazolines scaffolds 5a-f and 10a-d have been investigated. All the imidazolines-oxazolines derivatives were prepared from acid derivatives 1 and 6a-c, and enantiomerically pure (S)-2-amino-3-methyl-1-butanol in four steps with excellent optical purity. The structures of all newly synthesized compounds have been elucidated by $^1H$, $^{13}C$ NMR, GCMS, and IR spectrometry. Their purity was confirmed using elemental analysis. Some newly synthesized compounds were examined to in-vitro antimicrobial activity. Among the prepared products 10d was found to exhibits the most active against all tested bacteria and fungi with minimal inhibitory concentration (MIC) ranged between 21.9 and $42.6{\mu}g/mL$.

• Natural Product Sciences
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• v.16 no.1
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• pp.15-19
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• 2010

A new 2,7'-cyclolignan named lonicerinol (1) along with eight known lignans, (-)-epipinoresinol (2), (-)-pinoresinol (3), $9{\alpha}$-hydroxypinoresinol (4), 7R,8S-dihydrodehydrodiconiferyl alcohol (5), ($\pm$)-neo-olivil (6), (+)-isolariciresinol (7), 3-methoxy-8,4'-oxyneoligna-3',4,7,9,9'-pentol (8), and (-)-pinoresinol 4-O-glucoside (9), were isolated from the caulis of Lonicera japonica THUNB. (Caprifoliaceae). All of these constituents except for (-)-pinoresinol (3) and $9{\alpha}$-hydroxypinoresinol (4) are reported for the first time from the genus Lonicera. The structures and absolute configurations of these compounds were determined on the basis of spectroscopic analysis, including CD and 1D- and 2D-NMR techniques and chemical methods.

• Bulletin of the Korean Chemical Society
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• v.29 no.5
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• pp.953-958
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• 2008

A novel anthraquinone diamino-bridged bis($\beta$ -cyclodextrin) 2 was synthesized. The inclusion complexation behaviors of the native $\beta$ -cyclodextrin 1 and the novel bis($\beta$ -cyclodextrin) 2 with guests, such as acridine red (AR), neutral red (NR), ammonium 8-anilino-1-naphthalenesulfonate (ANS), sodium 2-(p-toluidinyl) naphthalenesulfonate (TNS) and rhodamine B (RhB) were investigation by fluorescence, circular dichroism and 2D NMR spectroscopy. The spectral titrations were performed in phosphate buffer (pH 7.20) at 25 ${^{\circ}C}$ to give the complex stability constants (Ks) and Gibbs free energy changes (−${\Delta}G^0$) for the stoichiometric 1:1 inclusion complexation of host 1 and 2 with guests. The results indicated that the novel bis($\beta$ -cyclodextrin) 2 greatly enhanced the original binding affinity of the native $\beta$ -cyclodextrin 1. Typically, bis($\beta$ -cyclodextrin) 2 showed the highest binding constant towards ANS up to 34.8 times higher than that of 1. The 2D NMR spectra of bis($\beta$ -cyclodextrin) 2 with RhB and TNS were performed to confirm the binding mode. The increased binding affinity and molecular selectivity of guests by bis($\beta$ -cyclodextrin) 2 were discussed from the viewpoint of the size/shape-fit concept and multipoint recognition mechanism.

• Natural Product Sciences
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• v.21 no.4
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• pp.255-260
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• 2015

Two new thiodiketopiperazines (TDKPs), designated graphiumins I (1) and J (2), were isolated from the culture broth of the marine-derived fungus Graphium sp. OPMF00224 by solvent extraction, silica gel column chromatography, and HPLC. Their absolute structures were elucidated by spectroscopic analyses (1D and 2D NMR data, ROESY correlations, and CD data) and chemical methods. They were found to be structurally rare TDKPs with a phenylalanine-derived indolin substructure. Compounds 1 and 2 inhibited yellow pigment production by methicillin-resistant Staphylococcus aureus (MRSA) with $IC_{50}$ values of 63.5 and $76.5{\mu}g/ml$, respectively, without inhibiting its growth, even at $250{\mu}g/ml$.

• Natural Product Sciences
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• v.24 no.3
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• pp.189-193
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• 2018

Chemical investigation of the ethyl acetate extract of Gibberella moniliformis JS1055 endophytic fungus derived from a halophyte, Vitex rotundifolia, led to the isolation of nine compounds including 7-butyl-6,8-dihydroxy-3(R)-pent-11-enylisochroman-1-one (1), 7-butyl-6,8-dihydroxy-3(R)-pentylisochroman-1-one (2), 7-butyl6,8-dihydroxy-3(R)-pentylisochroman-1-one (3), $5{\alpha},8{\alpha}$-epidioxyergosta-6,9(11),22-trien-3-ol (4), ergosterol peroxide (5), tetradecanoic acid (6), 8-O-methylfusarubin (7), nicotinic acid (8) and adenosine (9). They were identified by extensive spectroscopic data analysis including 1D, 2D ($^1H-^1H$ COSY, HSQC, HMBC) NMR, and ESIMS. All the isolates (1-9) are reported for the first time from this endophytic fungus.

• Journal of Applied Biological Chemistry
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• v.50 no.1
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• pp.13-16
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• 2007

Four compounds of previously known structures, friedeline (1), 3-hydroxyglutinol (2), p-hydroxy-benzealdehyde (3), and squalene (4) were obtained from the n-hexane- and EtOAc-soluble fractions of the dried whole plants of Sasa borealis. The structures of 1-4 were identified by the interpretation of their spectroscopic data including 1D and 2D NMR as well as by comparison with previously reported values. This is the first report on the isolation of compounds 1-4 from S. borealis.

• Natural Product Sciences
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• v.19 no.3
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• pp.258-262
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• 2013

Three ergosterol derivatives, ergosta-4,6,8(14),22-tetraen-3-one (1), ergosta-7,24(28)-dien-3-ol (2), and 5,8-epidioxyergosta-6,22-dien-3-ol(3) were isolated from the fruit body of Phellinus pini. Their structures were based on spectroscopic methods including IR, MS, and NMR (1D and 2D). These compounds were evaluated for their activity to decrease melanin production in ${\alpha}$-MSH (melanocyte stimulating hormone) activated B16F10 cells. Compound 1, 2, and 3 reduced melanin content in a dose-dependent manner at concentrations of 5~15 uM. They also suppressed the tyrosinase expression of protein and m-RNA level dose dependently by western blot analysis and RT-PCR experiment in B16F10 murine melanoma cells.

• Macromolecular Research
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• v.13 no.6
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• pp.467-476
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• 2005

The main objective of this study was to develop and characterize pH-sensitive biodegradable polymeric materials. For pH-sensitivity, we employed three kinds of moieties: 2-amino-3-(lH-imidazol-4-yl)-propionic acid (H), N-[4-( 4,6-dimethyl-pyrimidin-2ylsulfamoyl)-phenyl]succinamic acid (SM), and 2- {3-[ 4-( 4,6-dimethyl-pyrim­idin- 2-ylsulfamoyl)-phenylcarbamoyl]-propionylamino} -3-(3 H - imidazol-4-yl)-propionic acid (SH). The pH -sensitive diblock copolymers were synthesized by ring opening polymerization and coupling reaction from poly(ethylene glycol) (MPEG), $\varepsilon$-caprolactone (CL), D,L-lactide (LA) and pH-sensitive moieties. The pH-sensitive SH molecule was synthesized in a two-step reaction. The first step involved the synthesis of SHM, a methyl ester derivative of SH, by coupling reaction of SM and L-histidine methyl ester dihydrochloride, whereas the second step involved the hydrolysis of the same. The synthesized SM, SHM and SH molecules were characterized by FTIR, $^{1}H$-NMR and $^{13}C$-NMR spectroscopy, whereas diblock copolymers and pH-sensitive diblock copolymer were characterized by $^{1}H$-NMR and GPC analysis. The critical micelle concentrations were determined at various pH conditions by fluorescence technique using pyrene as a probe. The micellization and demicellization studies of pH-sensitive diblock copolymers were also done at different pH conditions. The pH-sensitivity was further established by acid-based titration and DLS analysis.

• Archives of Pharmacal Research
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• v.27 no.10
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• pp.1020-1022
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• 2004

A new ceramide alomacrorrhiza A was isolated from the ethanolic extract of the plant Alocasia macrorrhiza (L.) Schott. Its chemical structure was elucidated as (2S,3S,4R)-2N-[(2'R)-2'- hydroxy-hexacosanoyl]-tetradecane-1,3,4-triol based on extensive 1D, 2D NMR, EI-MS, FABMS, HR-FAB-MS spectroscopic data and chemical degradation studies.

• Journal of the Korean Society of Propulsion Engineers
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• v.23 no.5
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• pp.53-59
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• 2019

Solid fuel reacts with an oxidizer during combustion of a propellant to increase performance. Representative solid fuels are aluminum, cyclotrimethylenetrinitramine (RDX) and octahydro-1, 3,5,7-tetra nitro-1,3,5,7-tetrazocin (HMX). During combustion, these compounds generate white smoke by reacting with moisture and produce materials that are harmful to the environment, such as carbon monoxide, carbon dioxide, and methane gas. This study prepared a high-nitrogen-containing energetic material, hydrazinium 5-aminotetrazolate (HAT), which could be applied as a solid fuel. The compound was characterized by nuclear magnetic resonance (NMR) spectroscopy, and a thermal analysis was measured by differential scanning calorimetry (DSC). Also, the specific impulses and volumes of detonation gases were calculated using the EXPLO5 program.